Interview: Meet Rap's New Antihero, Fredo Santana

Who is Fredo Santana? The 23 year-old rapper doesn't really do interviews. He's earned a reputation for having a short fuse and gives zero fucks, especially when journalists ask him stupid questions. Still unsigned, he's not enamored by the spoils of the music industry and is wary of any kind of fawning.

His distrust is warranted. Hardened by his upbringing in Chicago -- dubbed "Chiraq" because of its similarity to wartime Iraq -- his tender age belies a life of battle scars. His lengthy rap sheet includes drug dealing as an adolescent and several jail stints and harkens back to the age of 12, when he was arrested for kicking down a bus door on Halloween. Even today, his brown eyes, separated by a small cross tattoo, often register an opaque vacancy. He's impossible to read.

After being name-checked in his cousin Chief Keef's cold-blooded "I Don't Like" in 2012, Fredo began taking rap seriously, releasing three mixtapes and one album just this year. The neophyte's "Jealous" with Kendrick Lamar (off his Trappin' Ain't Dead) is remarkably good and Drake personally asked him to star in "Hold On, We're Going Home." The menacing, albeit brief, music video cameo ranks as one of pop's most indelible images this year, no doubt spawning its share of nightmares.

Fredo hit another milestone by headlining his first New York City show at Santos Party House last week. Fans gathered on Lafayette Street for hours on a chilly night, many of them staying for the $100 meet-and-greet to get face time afterwards. As one journalist said to me during the show, the music was ancillary, the bigger deal was that the elusive rapper was actually here, in our city. The following day, Fredo invited Sound of the City to his Chelsea crash pad for a lengthy conversation.

You're notorious for not doing any press. This is rare that we're even speaking.
Yeah. I mean, I want to let my work talk for itself. I feel, I see everybody do interviews and they kill themselves. They don't be talking about shit and say things like, "I'm gonna do this classic!" and they don't deliver. I don't wanna talk about what I'm gonna do. I want it to be like, "Damn. I keep seeing Fredo but I don't really see him." Unless I get like a real, print issue.

Really? Most people think print is dead.It's important for me with my background. I'm not no backpack rapper. I'm a street rapper. I been locked up. My homies that's locked up. One of my homies just told me today, "Yo. They were saying your lyrics in Hip Hop Weekly for the 'Jealous' song." That's the biggest thing when you in jail is the music magazines. That's what gets us by. For all my homies that's locked up, facing like life and all that type of stuff, I want that for them.

There's a mystique about you. Between your reticence and public image, people misconstrue that into you're standoffish and creepy. You don't seem like that to me, but I guess I'm pretty scary.
Yeah. You could bring that vibe. I mean, yeah, I can get scary if someone trying to hurt me or my family. Other than that, nah. It started on my first album. From my first songs, it came off like that. I don't know. I can be just happy right now but soon as I go into the booth, I'm angry. You know? It's probably when I put the mic on and hear the beats, I think about my childhood and think of all the bad stuff. I don't know. I gotta be rapping about bad stuff.

Did you ever use art to escape the "bad stuff" as a kid?
I used to draw. I been drawing since like 5 years old. I stopped drawing and I guess, rapping came about. I've always been happy but I wasn't happy with the surroundings. My surroundings. My aunties and my mama and my neighbors. The community. Just the black community. The culture. How it just keep going and keep going. The poverty. All that. I wasn't happy with that.

At what age did you decide that you had to leave those surroundings?Probably at like 10. I was like, "Mama, what the fuck is going on?" I mean, she ain't got no money. So like 11 and 12, I started selling crack. I needed shoes and shit. I'm watching this on TV like, "I need this shit." I can't be wearing the same shoes, having holes in my shoes. So I started selling drugs to support myself.

What does selling drugs mean to an 11-year old? It started as a look out. Then you grow into knowing what you doing. It's up to you. You could work for other people or become a boss at a young age. You can buy your own work, wholesale, like anything else, and go sell it. I sold to family members and their friends and neighbors. I mean, somebody was gonna do it. Might as well keep it in the family. People grow up so fast. Real, real fast. By 12, I was buying my own socks, drawers, taking care of myself like a grown man.

At 23 years-old, you've already lived a lifetime.
Yeah. That's why I be chilling now. I smoke weed and just be chill. My brothers be on the same block. My mama still be over there. Ain't nothing really changed with the fame. I ain't never sign no deal. I'm still independent. Same thing's still same. Only thing, I don't like people seeing my face because they're like "Fredo this. Fredo that." They wanna take pictures and draw attention. Everybody else act different. Just treat me regular.

You have a lot of fans; even rappers seem to just want to hang around you.
Yeah. It's a role model thing. Like, I ran with their big brother or something. I'm a stand-up kind of guy. I'm a leader but I be laid back. I be in the studio working. I don't really try to kick it with rappers or try to hang.

The music industry was abuzz when Chief Keef got signed last year and then very quickly, they wrote him off. How did you perceive it?Yeah. Yeah. 100%, especially with what happened with the Chicago scene and the violence, everybody was like, "Aw." At the end of the day, he just turned 17 when that [all happened]. He just a little boy, you know?

Does that make you wary of being a part of the industry?Yeah. That too. That's what made me not want to do interviews too, 'cause of how they was like acting towards him. They wouldn't even let him be chill, like the way we chill right now. They were like trying to trick him or something. Don't trick him. Ask him real questions. Have a genuine conversation with him. They were like, trying to trick him into saying dumb stuff.

Keef's ascent brought a lot of talk of "cultural tourism" and the notion that people on the periphery were exploiting him. For instance, his Pitchfork interview (which was later retracted) distastefully took place at a gun range while he was on probation.That's why I don't really like doing interviews unless they genuinely want to do it and they genuinely want to write a story about me and push my moment and what I got to bring to hip-hop. Like, I dropped three mixtapes and an album this year.